Anticancer, antimicrobial activities of quinoline based hydrazone analogues: Synthesis, characterization and molecular docking

Katariya, Kanubhai D.; Shah, Shailesh R.; Reddy, D. Prabhakar

doi:10.1016/j.bioorg.2019.103406

Cited by 82 publications

(53 citation statements)

References 37 publications

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“…The most bio-effective complex against A. niger is the Cu 2+ complex (6), with IZ = 42 mm and AI = 114%, complexes (5)(6)(7)(8) are effective against C. albicans with IZ ranged from 33 to 50 mm and AI ranged from 103 to 156%, and the VO 2+ and Co 2+ complexes are effective against E. coli with IZ = 40 and 36 mm, with AI =114% and 103%, respectively. The other complexes showed T A B L E 1 Antimicrobial activities of the ligand (1) and its complexes (2)(3)(4)(5)(6)(7)(8) Figure 6. The enhancement of microbicide activity of some complexes could be illustrated basing on the Overtone's concept and Tweedy's chelation theory.…”

Section: Bactericidal and Fungicidal Activitiesmentioning

confidence: 99%

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

El‐Saied

Shakdofa

Al‐Hakimi

et al. 2020

Applied Organom Chemis

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complexes of a synthetic novel hydrazone containing a quinoline moiety were prepared. The composition and structure of the prepared compounds were elucidated by spectral and analytical techniques. The results reveal that all complexes were formed in 1:1 mole ratio except Mn 2+ and Cu 2+ complexes (3) and (7), which were formed in 1 M:2 L mole ratio. It was also found that the ligand binds the metal ions via NO donor sites as a monobasic bidentate chelator in all complexes through the enolic carbonyl oxygen and azomethine nitrogen atoms. The electronic absorption spectra and magnetic moment data demonstrated square pyramidal and octahedral geometries for the VO 2+ and Ni 2+ complexes, respectively, while the other complexes adopted tetrahedral geometry. The thermal decomposition of the complexes was discussed in relation to structure. The thermal analysis data demonstrated that all complexes were decomposed in one, two, three or four stages starting with the dehydration process, removal of coordination water molecules or elimination of anions and ended with the formation of the metal oxide. The bactericidal activities of the prepared compounds demonstrated that hydrazone (1) exerted a highly inhibitory effect against B. subtilis while VO 2+ , Co 2+ , and Cu 2+ complexes (2), (4), and (7) showed an inhibitory effect against E. coli more than the tetracycline. Additionally, the inhibitory effect of the prepared compound against A. niger showed that the Cu 2+ complex (6) is the most active while the Ni 2+ , Cu 2+ , and Zn 2+ complexes (5-8) exhibited an extremely inhibitory effect against C. albicans.

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Section: Bactericidal and Fungicidal Activitiesmentioning

confidence: 99%

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

El‐Saied

Shakdofa

Al‐Hakimi

et al. 2020

Applied Organom Chemis

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“…Further mechanistic study showed that compound 131 j was most potent among the series of active compounds by selective inhibition of topoisomerase I with GI 50 = 0.50 μM and also causes apoptosis in cancer cells, predicting its further use in the design of new, safe and potent anticancer drug (Scheme 27). [92]…”

Section: Quinoline-galactose Hybridsmentioning

confidence: 99%

Navigating the Synthesis of Quinoline Hybrid Molecules as Promising Anticancer Agents

Panda

Chakroborty

2020

ChemistrySelect

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The emergence of drug resistance and low specificity with side effects are the significant challenges in pharmaceutical sectors for control of cancer nowadays. Notwithstanding, this is an imperative prerequisite to develop novel anticancer agents through mainstream medicinal chemistry approaches. The intriguing quinoline and its derivatives have demonstrated as significant building blocks for the locating of new promising anticancer agents. Consequently, quinoline moiety with the addition of suitable congeners would offer a strategy for the development of potential drug candidates. This present review article summarizes the recent advances (2018‐2020) of quinoline hybrids and their anticancer activity. The mechanism action and plausible structure‐activity relationship have discussed.

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“…In order to explore the inhibitory capacity of all the prepared new mono and dipeptide-dihydroquinolinone conjugates (1)(2)(3)(4)(5)(6) have been evaluated by means of a stopped flow CO 2 hydrase assay against four human (h) CA isoforms (hCA I, hCA II, hCA IX and hCA XII). Inhibition results of the compounds are reported in Table 1, along with those referred to acetazolamide (AAZ), used as standard inhibitor.…”

Section: Carbonic Anhydrase Inhibitionmentioning

confidence: 99%

“…2-Quinolinones derivatives constitute a privilege class of heterocyclic compounds for their wide range of important biological properties such as such as antibacterial 1,2 , antimalarial 3 , antitumor 4 , carbonic anhydrase inhibitor 5,6 , antioxidant, anti-tuberculosis 7 , antiparasitic 8 and anti-hepatit C and B viruses activity 9 . For example, the 3,4-dihydro-2-quinolinone structure is found in a number of biologically active and FDA approved medicine such as cilostazol, carteolol and aripiprazole.…”

Section: Introductionmentioning

confidence: 99%

“…Synthesis and characterization of the new mono and dipeptide-dihydroquinolinone derivativesNew N-protected monopeptide and dipeptide-dihydroquinolinone conjugates(1)(2)(3)(4)(5)(6) were synthesised by the reaction of 7-amino-3,4dihydroquinolin-2(1H)-one with N-protected aminoacylbenzotriazole under microwave heating at 70 C for 30 min with good yields of 62-87%. The synthesis of the N-protected mono and dipeptide-dihydroquinolinone conjugates 1-6 is summarised in Scheme 1.The structures of N-protected mono and dipeptide-dihydroquinolinone conjugates (1-6) were elucidated by 1 H NMR, 13 C NMR, Synthesis pathways of the new dihydroquinolinone conjugates of N-protected amino acids and dipeptide.…”

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confidence: 99%

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Preparation, carbonic anhydrase enzyme inhibition and antioxidant activity of novel 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives incorporating mono or dipeptide moiety

Küçükbay

Gönül

Küçükbay

et al. 2020

Journal of Enzyme Inhibition and Medicinal Chemistry

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2020) Preparation, carbonic anhydrase enzyme inhibition and antioxidant activity of novel 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives incorporating mono or dipeptide moiety, ABSTRACT New dipeptide-dihydroquinolinone derivatives were successfully synthesised by benzotriazole mediated nucleophilic acyl substitution reaction and their structures were elucidated by spectroscopic and analytic techniques. The carbonic anhydrase (CA, EC 4.2.1.1) inhibitory activity of the new compounds was determined against four human (h) isoforms, hCA I, hCA II, hCA IX and hCA XII. While all compounds showed moderate to good in vitro CA inhibitory properties against hCA IX and hCA XII with inhibition constants in the micromolar level (37.7-86.8 and 2.0-8.6 mM, respectively), they did not show inhibitory activity against hCA I and hCA II up to 100 mM concentration. The antioxidant capacity of the peptide-dihydroquinolinone conjugates was determined using 1,1-diphenyl-2-picrylhydrazyl (DPPH) radical scavenging method. Most of the synthesised compounds showed low antioxidant activities compared to the control antioxidant compounds BHA and a-tocopherol. ARTICLE HISTORY

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Anticancer, antimicrobial activities of quinoline based hydrazone analogues: Synthesis, characterization and molecular docking

Cited by 82 publications

References 37 publications

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

Transition metal complexes derived fromN′‐(4‐fluorobenzylidene)‐2‐(quinolin‐2‐yloxy) acetohydrazide: Synthesis, structural characterization, and biocidal evaluation

Navigating the Synthesis of Quinoline Hybrid Molecules as Promising Anticancer Agents

Preparation, carbonic anhydrase enzyme inhibition and antioxidant activity of novel 7-amino-3,4-dihydroquinolin-2(1H)-one derivatives incorporating mono or dipeptide moiety

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